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Deadly Valentines: The Story of Capone's Henchman "Machine Gun" Jack McGurn and Louise Rolfe, His Blonde Alibi
Almost before the gunsmoke from the St. Valentine’s Day Massacre cleared, Chicago police had a Jack McGurn. They just couldn’t find him. McGurn, whose real name was Vincent Gebardi, was Al Capone’s chief assassin, a baby-faced Sicilian immigrant and professional killer of professional killers. But two weeks after the murders, police found McGurn and his paramour, Louise May Rolfe, holed up downtown at the Stevens Hotel. Both claimed they were in bed on the morning of the famous shootings, a titillating alibi that grabbed the public’s attention and never let go. Deadly Valentines tells one of the most outrageous stories of the 1920s, a twin biography of a couple who defined the extremes and excesses of the Prohibition era in America. McGurn was a prizefighter, professional-level golfer, and the ultimate urban predator and hit man who put the iron in Al Capone’s muscle. Rolfe, a beautiful blonde dancer and libertine, was the epitome of fashion, rebellion, and wild abandon in the new jazz subculture. They were the prototypes for decades of gangster literature and cinema, representing a time that has never lost its allure.
368 pages, Hardcover
First published January 1, 2012
4 people are currently reading
68 people want to read
About the author
Jeffrey Gusfield
1 book4 followersI learned my most important lessons about writing narrative history from my cousin, Pulitzer Prize winner Mackinlay Kantor (Mack wrote Andersonville, about the Confederate prison camp during the Civil War). I've been a dedicated Capone era researcher for over forty years, but my obsessive interest began when I was five, when famed Chicago photographer Anthony Berardi showed me a picture he took of the Saint Valentine's Day Massacre in 1929. I assume that most children would have been scarred; I was liberated.
I have a BFA from Drake University, where I learned from my mentor, Dr. W.S.E. "Doc" Coleman, that history was the best theater. I have an MLS from Lake Forest College, where my mentors Rosemary Cowler, Carol Gayle, and Dan LeMahieu reanimated my brain. My wife, Ann, and my son, Sam, are my other two-thirds.
I have a BFA from Drake University, where I learned from my mentor, Dr. W.S.E. "Doc" Coleman, that history was the best theater. I have an MLS from Lake Forest College, where my mentors Rosemary Cowler, Carol Gayle, and Dan LeMahieu reanimated my brain. My wife, Ann, and my son, Sam, are my other two-thirds.
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Displaying 1 - 12 of 12 reviews
November 12, 2013
Author Jeffrey Gusfield apparently knows not only where the bodies are buried, but also where they used to live or hang out. By actual count, there are at least 53 actual addresses listed within the pages of “Deadly Valentines,” places where Jack McGurn lived, “worked” or played. This reviewer has actually viewed all of those addresses using Google satellite maps and can verify their authenticity.
Gusfield reportedly spent more than four decades researching the history of McGurn or Vincent Gebardi, his real name. The author’s apparent purpose in revisiting the life of Al Capone’s most notorious assassin was to reveal the “humanity of (this) antihero” . . . in an attempt to “understand the person who lives under (his) costume.” In my view, the overall tone of this autobiography is one of near hero worship. Gusfield describes McGurn as “an immaculately dressed killer.” While admitting that McGurn “utilized his intelligence and talents for criminal gain . . . he still stands out as an amazing example of human achievement.” Really? The author claims, “As unfortunate as his choices may have been, one cannot deny the tremendous and lasting impact that he made on law, politics, popular culture and criminal endeavor.” Really? I guess you’ll just have to read the book for yourself to decide.
Apparently Capone’s hired gun and “his wayward middle-class minx, Louise Rolfe,” did influence Hollywood for a time. According to Gusfield, McGurn’s “words and especially his attitude will inspire the cinema gangsters. James Cagney, George Raft and Edward G. Robinson will continually attempt to reproduce Jack McGurn’s seemingly indomitable spirit and edgy demeanor.” As for Louise, McGurn’s so-called “Blonde Alibi” invents “gun-moll chic.” The author claims Louise’s persona “will eventually be reflected in movies from Hollywood as female stars attempt to mirror Louise’s combination of great style and practiced ennui.” Bonnie and Clyde were to come along just a bit later.
There are at least two take-away points from this story of Capone’s hired killer:
At one point, Jack McGurn is suspected in at least sixteen unsolved murders. Even though the gunmen often discarded their weapons at the crime scenes, even though fingerprint technology was being used, forensic evidence, if there was any, never convicted McGurn of any assassination. Authorities could only arrest him on vagrancy or concealed weapon charges. In the end, his own partners in crime became McGurn’s own judge, jury and executioner. I guess Jesus was right, “All who take the sword will perish by the sword.” (See Matthew 26:52)
Finally, it’s interesting to note that McGurn began his adult life as a promising, welterweight boxer. Gusfield notes, “He tastes a small bit of fame and glory with his first victories.” Later, his career path turns to murder and mayhem. Toward the end of his life, McGurn returns to the sport of tournament golf. He even qualifies to play in the prestigious Western Open. Talk about a plot twist! Years of blood and bullets sandwiched between two diametrically opposite professional sports. It gives a whole new meaning to Marlon Brando’s words in the 1954 film classic, “On the Waterfront.” Terry to Charlie: “I coulda had class. I coulda been a contender. I coulda been somebody.”
Gusfield reportedly spent more than four decades researching the history of McGurn or Vincent Gebardi, his real name. The author’s apparent purpose in revisiting the life of Al Capone’s most notorious assassin was to reveal the “humanity of (this) antihero” . . . in an attempt to “understand the person who lives under (his) costume.” In my view, the overall tone of this autobiography is one of near hero worship. Gusfield describes McGurn as “an immaculately dressed killer.” While admitting that McGurn “utilized his intelligence and talents for criminal gain . . . he still stands out as an amazing example of human achievement.” Really? The author claims, “As unfortunate as his choices may have been, one cannot deny the tremendous and lasting impact that he made on law, politics, popular culture and criminal endeavor.” Really? I guess you’ll just have to read the book for yourself to decide.
Apparently Capone’s hired gun and “his wayward middle-class minx, Louise Rolfe,” did influence Hollywood for a time. According to Gusfield, McGurn’s “words and especially his attitude will inspire the cinema gangsters. James Cagney, George Raft and Edward G. Robinson will continually attempt to reproduce Jack McGurn’s seemingly indomitable spirit and edgy demeanor.” As for Louise, McGurn’s so-called “Blonde Alibi” invents “gun-moll chic.” The author claims Louise’s persona “will eventually be reflected in movies from Hollywood as female stars attempt to mirror Louise’s combination of great style and practiced ennui.” Bonnie and Clyde were to come along just a bit later.
There are at least two take-away points from this story of Capone’s hired killer:
At one point, Jack McGurn is suspected in at least sixteen unsolved murders. Even though the gunmen often discarded their weapons at the crime scenes, even though fingerprint technology was being used, forensic evidence, if there was any, never convicted McGurn of any assassination. Authorities could only arrest him on vagrancy or concealed weapon charges. In the end, his own partners in crime became McGurn’s own judge, jury and executioner. I guess Jesus was right, “All who take the sword will perish by the sword.” (See Matthew 26:52)
Finally, it’s interesting to note that McGurn began his adult life as a promising, welterweight boxer. Gusfield notes, “He tastes a small bit of fame and glory with his first victories.” Later, his career path turns to murder and mayhem. Toward the end of his life, McGurn returns to the sport of tournament golf. He even qualifies to play in the prestigious Western Open. Talk about a plot twist! Years of blood and bullets sandwiched between two diametrically opposite professional sports. It gives a whole new meaning to Marlon Brando’s words in the 1954 film classic, “On the Waterfront.” Terry to Charlie: “I coulda had class. I coulda been a contender. I coulda been somebody.”
June 17, 2012
Jack McGurn comes alive in "Deadly Valentines" and not in the sense of resurrection, but as the child who sees the Statue of Liberty for the first time. Rather than focusing on the man who became Jack McGurn (The Criminal), you get a real picture of what life was like during his earlier years. Assuming that people are a product of their environments, it was easy to see the road he chose to follow. Being interested in what makes people tick, I felt a certain amount of understanding and maybe compassion for Jack and Lulu. She was an entirely different breed of woman than what we've seen portrayed during this era. Her character was engaging and as in Jack, you could feel the darkness that lingered inside of them. Like another reviewer mentioned, they were flawed. As a reader, I accepted this fact and as a flawed person myself (as we all are), I saw this journey as a life lesson. This life lesson also happened to be a significant historical lesson as well and isn't that what it's all about?
Kudos to Jeff Gusfield for sharing this passionate story with the rest of us!
Kudos to Jeff Gusfield for sharing this passionate story with the rest of us!
September 6, 2016
This is a very good read for those with an interest in old time Chicago gangster stories. Goes through the life and times of “Machine Gun” Jack McGurn. Also does a back and forth with the life and times of his famous “Blonde Alibi” Louise Rolfe.
Pretty solid details for one of Capone’s top henchmen and a mass murderer. Pretty interesting character in his pursuit of a pro golf career and his dedication to Capone.
I really liked this read and the background it provides with an accurate, clear timeline and corrects many of the misconceptions sometimes connected to the subject.
Pretty solid details for one of Capone’s top henchmen and a mass murderer. Pretty interesting character in his pursuit of a pro golf career and his dedication to Capone.
I really liked this read and the background it provides with an accurate, clear timeline and corrects many of the misconceptions sometimes connected to the subject.
July 24, 2012
This was a really fun read, despite the fact that almost everyone in the book gets 'offed' at some point. It's non-fiction, but reads like fiction. If you liked the series The Sopranos, you will probably like this book...
August 24, 2016
The good old days of Capone and Omerta and the Roaring Twenties!
November 2, 2021
In spite of all the gun violence, I had to keep reading to the end. The author has done an incredible job of researching the era and the gangsters who were so active.
August 21, 2016
What America accomplished with the banning of alcohol – the start of Prohibition – during the 1920’s and early ‘30’s, was not turning the nation into a “dry” country, but instead providing the groundwork for the formation and growth of organized crime. The money made from the sale of illegal liquor gave rise to criminal organizations in most cities, and the competition to benefit from its sale led to numerous murders; in a city, such as Chicago, where Jack McGurn plied his trade, gangsters brazenly killing one another on the streets seemed to be a daily occurrence.
As long as the gangsters killed one another the citizenry was troubled but tolerant, that was until Chicago boss Al Capone pushed it too far and on February 14, 1929 orchestrated the St. Valentine’s Day Massacre, in which seven men, some of them members from a rival organization (others just unlucky to be there), were lined up against a wall in a Chicago garage and machine gunned and shot gunned to death. Shot in the back, and murdered together, this crime tested the nation’s tolerance for gangsters and killing, and began the downfall of Capone and McGurn.
While a biography on “Machine Gun” Jack McGurn, who quickly rose in Capone’s ranks to become his main enforcer and assassin, would be of interest to those who enjoy studying gangsters of old alone, it is his assumed involvement in planning and executing the St. Valentine’s Day Massacre (Capone was in Florida on the fateful day) that makes his story, and many others who claim involvement, of true interest to crime historians.
In telling McGurn’s tale, from his early days trying to make it as a prizefighter, to his rise in the Capone organization, where his penchant for planning murders with precision and intelligence made him extremely effective, author Gusfield also relates the life of Louise Rolfe, the uncontrollable and fame-obsessed young woman who first became his “Blonde Alibi” for the morning of the Massacre, and eventually his wife. While her tale is interesting, it is secondary to his.
Nobody knows for certain who took part in the St. Valentine’s Day Massacre, and there have been many books claiming to be the final word on the matter. Although Rolfe provided McGurn with an alibi for that morning, many believe McGurn, along with Tony “Joe Batters” Accardo (later to head the Chicago Outfit) were the main shooters, accompanied by some out-of-town gangsters (necessary to fool the doomed men into believing they were actually police officers). Gusfield believes McGurn would have been unable to pass up the chance to take revenge on the Gusenberg brothers, Frank and Peter, who had tried to kill him previously, putting him in the hospital with bullet wounds, including one to the lungs.
There are many theories on the St. Valentine’s Day Massacre (in another book, Get Capone, that author even theorizes the Capone organization had nothing to do with it whatsoever), and Gusfield covers a lot of them.
The Massacre changed everything, having tested the public’s tolerance for bloodshed, and led to Capone’s downfall, and as such, McGurn’s. Having been sent to jail for tax evasion (Eliot Ness and his band of Untouchables had nothing to do with that; while the Kevin Costner film was enjoyable, it should be viewed as a complete work of fiction, with very little historical accuracy), Frank Nitti became the visible head of The Outfit (he wasn’t thrown off a roof and killed like in the Costner film), and had never been a fan of McGurn’s, thus putting the gangster out of favor with The Outfit.
What’s truly fascinating about McGurn was the fact that at some point after the Massacre he tried to go straight and become a golf pro. Apparently, the athletic McGurn was exceptionally good at the sport, and if it wasn’t for the fact his reputation as a killer made him a constant target for police harassment, he might have just accomplished his goal, and was on his way to doing so when arrested for vagrancy.
McGurn’s is the standard gangster life, the rise and the inevitable fall, and the eventual death as a product of the violence he himself had meted out over the years. McGurn is likeable in Gusfield’s account, which is always the trick when reading about gangsters; while McGurn is likeable, and others like Capone, “Lucky” Luciano, “Bugsy” Siegel and John Gotti can come off as likeable; the fact still remains that if most were given a psyche evaluation, we’d discover they qualify as psychopaths.
Deadly Valentines is an excellent read, telling a compelling story of a gangster who hasn’t received as much attention historically as others, but is still a fascinating man, which is something to say in that during the time in which McGurn operated, the world of gangsters was full of interesting and unique characters that seemed larger than life. A MUST read for those interested in the era and gangsters, and a wonderful read for those looking to explore the same for the first time.
As long as the gangsters killed one another the citizenry was troubled but tolerant, that was until Chicago boss Al Capone pushed it too far and on February 14, 1929 orchestrated the St. Valentine’s Day Massacre, in which seven men, some of them members from a rival organization (others just unlucky to be there), were lined up against a wall in a Chicago garage and machine gunned and shot gunned to death. Shot in the back, and murdered together, this crime tested the nation’s tolerance for gangsters and killing, and began the downfall of Capone and McGurn.
While a biography on “Machine Gun” Jack McGurn, who quickly rose in Capone’s ranks to become his main enforcer and assassin, would be of interest to those who enjoy studying gangsters of old alone, it is his assumed involvement in planning and executing the St. Valentine’s Day Massacre (Capone was in Florida on the fateful day) that makes his story, and many others who claim involvement, of true interest to crime historians.
In telling McGurn’s tale, from his early days trying to make it as a prizefighter, to his rise in the Capone organization, where his penchant for planning murders with precision and intelligence made him extremely effective, author Gusfield also relates the life of Louise Rolfe, the uncontrollable and fame-obsessed young woman who first became his “Blonde Alibi” for the morning of the Massacre, and eventually his wife. While her tale is interesting, it is secondary to his.
Nobody knows for certain who took part in the St. Valentine’s Day Massacre, and there have been many books claiming to be the final word on the matter. Although Rolfe provided McGurn with an alibi for that morning, many believe McGurn, along with Tony “Joe Batters” Accardo (later to head the Chicago Outfit) were the main shooters, accompanied by some out-of-town gangsters (necessary to fool the doomed men into believing they were actually police officers). Gusfield believes McGurn would have been unable to pass up the chance to take revenge on the Gusenberg brothers, Frank and Peter, who had tried to kill him previously, putting him in the hospital with bullet wounds, including one to the lungs.
There are many theories on the St. Valentine’s Day Massacre (in another book, Get Capone, that author even theorizes the Capone organization had nothing to do with it whatsoever), and Gusfield covers a lot of them.
The Massacre changed everything, having tested the public’s tolerance for bloodshed, and led to Capone’s downfall, and as such, McGurn’s. Having been sent to jail for tax evasion (Eliot Ness and his band of Untouchables had nothing to do with that; while the Kevin Costner film was enjoyable, it should be viewed as a complete work of fiction, with very little historical accuracy), Frank Nitti became the visible head of The Outfit (he wasn’t thrown off a roof and killed like in the Costner film), and had never been a fan of McGurn’s, thus putting the gangster out of favor with The Outfit.
What’s truly fascinating about McGurn was the fact that at some point after the Massacre he tried to go straight and become a golf pro. Apparently, the athletic McGurn was exceptionally good at the sport, and if it wasn’t for the fact his reputation as a killer made him a constant target for police harassment, he might have just accomplished his goal, and was on his way to doing so when arrested for vagrancy.
McGurn’s is the standard gangster life, the rise and the inevitable fall, and the eventual death as a product of the violence he himself had meted out over the years. McGurn is likeable in Gusfield’s account, which is always the trick when reading about gangsters; while McGurn is likeable, and others like Capone, “Lucky” Luciano, “Bugsy” Siegel and John Gotti can come off as likeable; the fact still remains that if most were given a psyche evaluation, we’d discover they qualify as psychopaths.
Deadly Valentines is an excellent read, telling a compelling story of a gangster who hasn’t received as much attention historically as others, but is still a fascinating man, which is something to say in that during the time in which McGurn operated, the world of gangsters was full of interesting and unique characters that seemed larger than life. A MUST read for those interested in the era and gangsters, and a wonderful read for those looking to explore the same for the first time.
April 15, 2012
My grandfather grew up in Chicago in the late 1920s and 1930s. He once described how he would play gangsters as a little boy, until the St. Valentine's Day Massacre. Then it just got too real, and too scary. The St. Valentine's Day Massacre went down in history as the epitome of the violence of the bootlegger wars, and had a lasting effect on the country. Al Capone was one of the central figures involved. However, I didn't know much more than that going into this book. Now I can say that I have a good grasp of not only the Massacre, but the people behind it and the general atmosphere of the day.
Gusfield seems to have a conflicted view of Jack McGurn in Deadly Valentines. On one hand, McGurn was a ruthless killer, a general in Al Capone's crime outfit who would not hesitate to kill. Gusfield doesn't shy away from that fact. But he also seems to admire McGurn. He often focuses on McGurn's athletic prowess, first as a boxer and later as a golfer. He also is sympathetic to McGurn's desire to kill the men who gunned down his step-father. Through Gusfield's narration, we are presented with a well-rounded hero/villain. Gusfield isn't nearly as kind to Louise Rolfe, who is presented as a manipulative, selfish jazz baby. It's a little funny that the man who killed countless people during the Prohibition bootlegger wars comes across as so much more likable than his "blond alibi."
Overall, Deadly Valentines is very readable. There are photographs throughout the book of the characters who are in play. Squeamish readers should be warned that there are crime photographs of people who have been shot to death. The names can get confusing at times, but that's because criminals presented used so many alibis and nicknames. Gusfield did a pretty good job keeping things together from that point of view. Sometimes he made some assumptions and guesses in the narration, rather than sticking straight to the facts. He addresses this and his reasons and method for doing it, but I think strict history buffs still might take issue with it.
If you're at all interested in the history of Prohibition, Al Capone, the Great Depression, the Roaring Twenties, or the St. Valentine's Day Massacre, this is a book you'll want to read.
Gusfield seems to have a conflicted view of Jack McGurn in Deadly Valentines. On one hand, McGurn was a ruthless killer, a general in Al Capone's crime outfit who would not hesitate to kill. Gusfield doesn't shy away from that fact. But he also seems to admire McGurn. He often focuses on McGurn's athletic prowess, first as a boxer and later as a golfer. He also is sympathetic to McGurn's desire to kill the men who gunned down his step-father. Through Gusfield's narration, we are presented with a well-rounded hero/villain. Gusfield isn't nearly as kind to Louise Rolfe, who is presented as a manipulative, selfish jazz baby. It's a little funny that the man who killed countless people during the Prohibition bootlegger wars comes across as so much more likable than his "blond alibi."
Overall, Deadly Valentines is very readable. There are photographs throughout the book of the characters who are in play. Squeamish readers should be warned that there are crime photographs of people who have been shot to death. The names can get confusing at times, but that's because criminals presented used so many alibis and nicknames. Gusfield did a pretty good job keeping things together from that point of view. Sometimes he made some assumptions and guesses in the narration, rather than sticking straight to the facts. He addresses this and his reasons and method for doing it, but I think strict history buffs still might take issue with it.
If you're at all interested in the history of Prohibition, Al Capone, the Great Depression, the Roaring Twenties, or the St. Valentine's Day Massacre, this is a book you'll want to read.
July 11, 2012
"Deadly Valentines ..." is a good story about Al Capone's number one boy "Machine Gun" Jack McGurn and Jack's girlfriend Louise Rolfe. It covers Chicago in the Roaring 20's and the birth of organized crime. People interested primarily in the St. Valentine's Day Massacre might be disappointed that the book doesn't go into greater detail than it does about that event. The Massacre is a watershed event and is given its due, but there is so much else happening around Jack and Louise, who could be posterchildren for Roaring 20's Chicago. It's a very good intro to all the players in the North and South Side mobs, the Chicago police and politicians. Jack's rise and fall covers the arc of many a gangster who rides high for a while, but inevitably has to fall.
The most intriguing person is Louise Rolfe. An attractive blonde party girl, she and Jack seem to have made a real connection. She lived to the ripe old age of 88, dying in 1995. It's unfortunate Louise didn't write a book, but she kept her mouth shut all those years and took her secrets with her.
The most intriguing person is Louise Rolfe. An attractive blonde party girl, she and Jack seem to have made a real connection. She lived to the ripe old age of 88, dying in 1995. It's unfortunate Louise didn't write a book, but she kept her mouth shut all those years and took her secrets with her.
December 21, 2013
Really didn't finish it. Got about half through and quit. The research on this book was amazing and excellent. I loved all the information about Chicago. The amount of violence and death was just too much. I might pick it up and finish it sometime. It was a library book, I had renewed it twice and didn't want to keep going.
October 2, 2012
Goood story, trouble deciding whether it is history of Capone or Jack and Louise...because it starts out about the relationship, but loses steam, focus. Interesting though....One typo on footnote number size/font.
May 9, 2012
Good, but not what I was after. More a double biography than the story of the valentine's day massacre.
Displaying 1 - 12 of 12 reviews